Sequential one-pot three-step synthesis of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazole systems
| Autor: | Marcos A. P. Martins, Carson W. Wiethan, Helio G. Bonacorso, Nilo Zanatta, Alex Ketzer, Gean M. Dal Forno, Clarissa P. Frizzo, Mark Stradiotto |
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| Rok vydání: | 2017 |
| Předmět: |
1
2 3-Triazole Trifluoromethyl 010405 organic chemistry General Chemical Engineering Substituent Sonogashira coupling General Chemistry Pyrazole 010402 general chemistry 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry.chemical_compound chemistry XPhos Organic chemistry Moiety |
| Zdroj: | RSC Advances. 7:43957-43964 |
| ISSN: | 2046-2069 |
| Popis: | This work reports a successful one-pot three-step protocol for the synthesis of a new series of 15 examples of polysubstituted 4-(5-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-1,2,3-triazoles, in which sequential Sonogashira cross-coupling, desilylation, and a copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) with an overall yield of up to 72% were used. The presence of a trifluoromethyl substituent attached to the pyrazole moiety made the Sonogashira cross-coupling reaction challenging. Additionally, the selection of the ancillary ligand XPhos was essential and indispensable for the desired heterocyclic construction. |
| Databáze: | OpenAIRE |
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